Is parking easy in Oregon, WI?

As of early 2026, 94% of users say parking is easy

Is Oregon, WI dog-friendly?

As of early 2026, 94% of users say it's dog friendly

Does Oregon, WI have sidewalks?

As of early 2026, 92% of users say there are sidewalks

Do kids play outside in Oregon, WI?

As of early 2026, 87% of users say kids play outside

Would people walk alone at night in Oregon, WI?

As of early 2026, 86% of users say people would walk alone at night

Are yards well-kept in Oregon, WI?

As of early 2026, 85% of users say yards are well-kept

Is a car needed in Oregon, WI?

As of early 2026, 84% of users say car is needed

Are the streets well-lit in Oregon, WI?

As of early 2026, 80% of users say streets are well-lit

Does Oregon, WI show holiday spirit?

As of early 2026, 80% of users say there's holiday spirit

As of early 2026, 77% of users say it's quiet

Is Oregon, WI walkable to restaurants?

As of early 2026, 68% of users say it's walkable to restaurants

Do residents of Oregon, WI plan to stay at least 5 years?

As of early 2026, 68% of users say they plan to stay for at least 5 years

Are neighbors friendly in Oregon, WI?

As of early 2026, 68% of users say neighbors are friendly

Is there wildlife in Oregon, WI?

As of early 2026, 58% of users say there's wildlife

Is Oregon, WI walkable to grocery stores?

As of early 2026, 48% of users say it's walkable to grocery stores

Are there community events in Oregon, WI?

As of early 2026, 43% of users say there are community events

OFF MARKET

4569 County Highway B
Oregon, WI 53575

3 Beds
2 Baths
2,400 sqft (on 4.31 acres)

$527,300

Trulia Estimate

as of Jul 23, 2026

Est. Refi. Payment $3,425/mo*

Refinance Your Home

$527,300

Trulia Estimate

as of Jul 23, 2026

Est. Refi. Payment $3,425/mo*

Refinance Your Home

3 Beds

2 Baths

2,400 sqft

(on 4.31 acres)

Local Information

Map ViewExplore the area around 4569 County Highway B.
Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1880

Lot Size

4.31 acres

Living Area

2,400 sqft

Price/Sqft

$220

Parking

Garage

Description

Have your own piece of the pie! This 4.31 acres of lush landscape can be yours and located just minutes from Madison! 1880's farmhouse offers country style kitchen with island, large living room, 3 season room , master bedroom, full bath and laundry on main level w/ washer & dryer incl., plus two bedrooms and second bath on upper level. Basement is partially finished and ample storage too. Detached 24X40 garage, heated with nat. gas for work space plus two car stalls.

4569 County Highway B, Oregon, WI 53575 is a 3 bedroom, 2 bathroom, 2,400 sqft single-family home built in 1880. It last sold for $242,000 on Nov 3, 2017. It is currently off market. The Trulia Estimate is $527,300, with a rent estimate of $2,714/month.

Home Details for 4569 County Highway B

Interior Features
Interior Details BasementAtticNumber of Rooms: 8Types of Rooms: Family Room, Laundry Room, Mud Room
Levels, Entrance, & Accessibility Stories: 2Floors: Carpet, Hardwood, Laminate
Appliances & Utilities Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleDeckExterior: VinylGardenLawnPorch
Parking & Garage GarageParking Spaces: 2Parking: Garage Detached

Property Information
Year Built Year Built: 1880Year Updated: 1992
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial

Community
Units in Building: 1

Lot Information
Lot Area: 4.31 acres

Additional Information
Greenhouse

Price History for 4569 County Highway B

Date	Price	Event	Source
11/03/2017	$242,000	Sold	N/A
Recording Date 11/03/2017 Contract Date 10/31/2017 County Transfer Tax N/A Total Transfer Tax $726
10/14/2016	$249,900	ListingRemoved	Agent Provided

04/27/2016	$249,900	Listed For Sale	Agent Provided

10/02/2015	$249,900	ListingRemoved	Agent Provided

05/13/2015	$249,900	PriceChange	Agent Provided
Price Change $20,000 (-7%)
11/19/2014	$269,900	PriceChange	Agent Provided
Price Change $5,000 (-2%)
10/29/2014	$274,900	PriceChange	Agent Provided
Price Change $5,000 (-2%)
07/23/2014	$279,900	Listed For Sale	Agent Provided

Market trends in Oregon

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

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Property Tax and Assessment

Year	2024
Tax	$5,376
Assessment	$429,200

Home facts updated by county records

Comparable Sales for 4569 County Highway B

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
2122 Sand Hill Rd, Oregon, WI	0.50	Single-Family Home	$255,000	11/19/25	3	1	1,768
4644 Willow Pass, Oregon, WI	0.48	Single-Family Home	$457,500	07/06/26	3	2	2,229
4365 Schneider Dr, Oregon, WI	0.91	Single-Family Home	$625,000	05/27/26	3	3.5	2,100
1864 County Road Mm, Oregon, WI	1.27	Single-Family Home	$355,000	08/15/25	3	2	952
2000 Timber Lake Rd, Oregon, WI	0.91	Single-Family Home	$860,000	10/23/25	4	3.5	4,007
1903 County Highway Mm, Oregon, WI	1.34	Single-Family Home	$880,000	07/07/26	2	3.5	3,292
2073 Hawkinson Rd, Oregon, WI	1.78	Single-Family Home	$525,000	05/01/26	4	2	1,728
4266 Pella Ln, Mc Farland, WI	1.40	Single-Family Home	$402,500	11/06/25	3	2	1,272
2460 Hillpoint Rd, Mc Farland, WI	1.67	Single-Family Home	$425,000	08/19/25	3	2	1,923
4689 Holm Rd, Oregon, WI	1.70	Single-Family Home	$510,000	04/14/26	3	2	1,946

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $456,600
3 bd
2 ba
1,820 sqft
2221 Southview Rd,
Oregon, WI 53575
OFF MARKET
Est. $454,400
3 bd
2 ba
2,497 sqft
4641 County Road B,
Oregon, WI 53575
OFF MARKET
Est. $539,100
4 bd
2 ba
2,273 sqft
4663 County Road B,
Oregon, WI 53575
OFF MARKET
Est. $498,600
4 bd
2 ba
2,226 sqft
2291/2293 White Oak Trl,
Oregon, WI 53575
OFF MARKET
Est. $649,700
4 bd
2.5 ba
3,440 sqft
4655 County Road B,
Oregon, WI 53575
OFF MARKET
Est. $462,600
4 bd
2.5 ba
2,182 sqft
2299 White Oak Trl,
Oregon, WI 53575
OFF MARKET
Est. $571,400
5 bd
3.5 ba
4,276 sqft
2412-2414 White Oak Trl,
Oregon, WI 53575
SOLD
JUL 6, 2026
$457,500
3 bd
2 ba
2,229 sqft
4644 Willow Pass,
Oregon, WI 53575
OFF MARKET
Est. $1,418,600
2 bd
2 ba
2,017 sqft
4452 County Road B Rd,
Oregon, WI 53575
Rich Diamond's Open Bid Auct., Closed
OFF MARKET
Est. $560,600
4 bd
3 ba
3,235 sqft
2315 White Oak Trl,
Oregon, WI 53575
SOLD
NOV 19, 2025
$255,000
3 bd
1 ba
1,768 sqft
2122 Sand Hill Rd,
Oregon, WI 53575
OFF MARKET
Est. $467,000
3 bd
2 ba
2,196 sqft
2399 White Oak Trl,
Oregon, WI 53575

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Additional Cost

Assigned Schools

These are the assigned schools for 4569 County Highway B.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Oregon

At least 64 Trulia users voted on each feature.

94 % Say parking is easy
94 % Say it's dog friendly
92 % Say there are sidewalks
87 % Say kids play outside
86 % Say people would walk alone at night
85 % Say yards are well-kept
84 % Say car is needed
80 % Say streets are well-lit
80 % Say there's holiday spirit
77 % Say it's quiet
68 % Say it's walkable to restaurants
68 % Say they plan to stay for at least 5 years
68 % Say neighbors are friendly
58 % Say there's wildlife
48 % Say it's walkable to grocery stores
43 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Tanya Hoppe
Resident
2y ago
"Friendly and family orientated little Town with great school district. Our neighbors are great and watch out for each other. "
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Khockett58
Resident
5y ago
"Village Oregon Great place to live. Great schools & sport Great food places to eat. Doctor clinics Gad stations Banks. Small town but close to drive in to Madison or Stoughton And other cities "
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Lysagrant
Resident
5y ago
"15 minute drive from Madison. No public transportation. Easy access to rate 14. Not much traffic even at rush hour."
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Tjrbackstroker
Visitor
6y ago
"A quick drive up to Madison. The area is very drivable with not too much traffic. It is very easy to get on the highway."
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Kelly J. P.
Resident
6y ago
"Love it here! Best move to call this home for our family to grow. Super nice community. We love our neighbors and enjoy to small town feel that Oregon has to offer & also super close to Madison for fun nights out!"
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Ken D.
Resident
7y ago
"Great schools, convenient to madison, stoughton and Fitchburg. Housing market is booming, low crime"
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Rachel
Resident
7y ago
"To always keep an eye on your kids no matter how safe a neighborhood is deemed to be. Oregon is a great place to live!"
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miltydog
12y ago
"Wonderful schools and a strong sense of community"
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Donna R. B.
12y ago
"Very private rural subdivision....may be a longer drive to madison but for the beautiful lot and privacy a huge bonus"
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Stevie K.
12y ago
"If you like your privacy, multi level living, looking out the back you feel as if you are in the woods! Lots of updates and well cared for. Great neighbors, I used to be one but moved out West, so I have personally been inside and it's great! It is located on a private circle with little traffic! It's definitely a must see!"
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Stefan
13y ago
"This area of Oregon is excellent. The schools are the best. The neighborhoods around Lincoln Road, County A and Hillcrest are nice, but, drivers have no regard for safety at all. Stay off these roads if you bike or run. Farm families are very nice, too. You will love bringing up children in this area. Oregon is the best community in the Madison area for kids and your families to live."
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